Claire: anal, then he slips into the "wrong" hole

“Let me fuck you, Claire, please,” he groans. "I don't want to be a virgin."

His legs are parted, and I can still see his shiny, swollen butthole winking at me after I destroyed it, making his request to fuck me even more comical.

I scoff. "I just popped your cherry. You're not a virgin."

"You know what I mean," he counters.

"The deal was for a blow job. Mine are pretty good, so you should take what you get."

"I know. Just thought I should try."

Shit. I shouldn't have told him I took the dildo in my ass. But, it does sound fun. I like being the more experienced one for once. I’ve never been anyone’s first at anything.

I smirk and unstrap and put the harness and dildo on the pillow. “You're a natural bottom, Tyler. Do you really want to penetrate me, or are you just forcing the interest?"

He laughs, propping himself up on his elbows, his face still flushed. His eyes feast on my big pussy lips now that the harness is gone. His cock is rock hard. "I definitely want to fuck you. I promise. You won't give me the pussy, so..."

"You want my butthole," I reply. "It's a fair request, and I'm not virgin there at least," I admit. I squirt some of the lube on my fingers and spread it on his cock.

I've only been fucked in the ass once. That was Matt's much thicker penis. I've also been using the Outlaw and other toys on the regular, so I know I can fit Tyler without much warmup. "I'll let you fuck my ass. I'm really trusting you. Stay out of my front hole. And even though it's anal, don't come inside me. Okay?" He nods. "Trade places with me."

I get on my hands and knees, and Tyler mounts me. "Find the right hole, please. That's really important," I say. He presses the tip against my anus. "Yes." I bear down to take him in, and he's in me to the hilt easily: warm, full, stretching in that familiar way.

"Fuck yeah," he groans.

"Congratulations," I say. "Start slow. Don't come too fast."

I grip him with my muscles and let him go to work. He starts thrusting, tentative at first, then steadier as he finds his rhythm. I rock back to meet him. The taboo flips hard, and I slip back into the more familiar submissive Claire, which feels even hotter after dominating him so thoroughly just minutes ago.

I'm getting fucked in the ass and taking a man's virginity. That's pretty cool.

My virgin lover is having the time of his life. He doesn’t hold back his praise, and I eat it up. His pace escalates quickly. He slaps my ass twice, and my heavy tits are flopping with the dull thud every time he drives into my butt cheeks. I pretend I am still in charge, directing things, telling him what to do, but I'm not the dominant anymore. Tyler is in control and owns me. Being the boss lady was fun, but submissive church girl Claire is back and loving it.

I should have been doing more anal all along. I've been missing out. Maybe with a condom next time, but this feels amazing. Ramya would say it doesn't add to my body count.

Tyler gets bolder and pulls all the way out after each thrust, leaving my butthole hanging open and empty as best he can with his girth. His hands part my cheeks, exaggerating the effect. My anus twitches, closing part-way, then relaxing into its open, distended state. I have no control of my bowels, and it's hot and submissive.

I scoff. "Are you gaping me?"

"Yeah," he chuckles. "Is that cool?"

My butthole is stretched open and lewdly on display. "I guess. Feels weird."

I'm fully relaxed now, and my anus has a much looser grip on his cock compared with his first thrusts. Tyler's hands are back at my waist, but he's pulling out all the way until just the tip is in or against me, so he can rub the sensitive front underside of his cock against what little tightness I have left at the muscles guarding the opening. I time a clench with each re-entry, trying to close the gap and grip as best I can with fatigued, loosened muscles, but it won't be enough to make him come. I might have to finish him off with my mouth.

Then everything changes. The head slips out, I push back, and maybe I subconsciously arch my back to guide him lower to satisfy a deeper craving, I don't know, but the angle has changed slightly. He pushes in, and the head mashes lower against my perineum, then slides down until it reaches the pursed end of my slit, finds me wet and ready, and glides right into my soaked pussy!

I'm tighter there, but there's almost no resistance. I’m so wet from the rush, and my hymen is stretched a little from my dilator kit. Slim Tyler sinks balls-deep into my virgin pussy.

Holy shit.

I just lost my virginity.

I freeze in surprise at the fullness, at the lack of expected pain, and the sudden jolt of pleasure.

He feels it too.

Pump. Pump.

"Tyler!"

Pump.

"Wai-"

Pump.

He's fucking my virgin pussy!

I try to scoot forward, but his hands hold me in place.

Pump. Pump.

The stretch is real and very welcomed. My walls flutter around him, pleasure spiking sharp and sudden. It’s overwhelming, intimate, alive in a way toys never are. For just a second, I almost let him continue.

"Stop!"

Pump.

He freezes, cock fully embedded.

"That's my pussy. Get out now," I command.

He groans, voice breaking. “Shit, Claire, sorry."

The heat, tighter grip, and overall awesomeness of knowing he's in my virgin pussy is too much for his control, and he shoots past his point of no return.

He lets go of my hips completely, like his brain short-circuits. I drop forward onto the mattress, ass still up. Hot, sticky jets of semen rocket out of his little cock and paint my butt cheeks and lower back.

"Arggh! Coming!" he shouts.

Spurt after spurt coats my butt and back. It's a gigantic load, way out of proportion to his modest size. Tyler has some impressive potency.

I turn to my back, spreading sticky semen all over my sheets as another glob lands on my belly. “You fucking idiot,” I snap, half angry, half breathless. “I told you to stay out of my pussy!”

He’s shaking, breathing ragged. “I’m sorry… your pussy just… felt too good.”

I stay there as he finishes milking his cock onto my belly, heart hammering, processing. “Shit… you just took my virginity. I'm fucking pissed! I told you to be careful.”

He looks on the verge of panic. “Claire, I swear it was an accident. I didn’t mean...”

I scoff and reach over to my nightstand, pull out the #6 dilator, one step below the highest size Ramya used on me. "Are you smaller than this?" I sit up and hold it next to him before he goes soft. He's smaller, probably a #5. I slip a finger into my pussy, run it along the lips, wipe it on my sheets. No blood. "Do you see any blood?"

He looks closer at his cock, shakes his head no.

"You're slimmer than the toy I use. You didn't pop my cherry at least. But that was full penetration. You fucked my pussy. It still counts, even though it was only for a few seconds. Shit."

"Sorry," he says. "Felt really good, if that helps," he adds with a lame laugh.

Yeah. It felt good for me, too.

I lie there thinking: That accidental slip, the way he lost it after just a few thrusts because my pussy felt “too good”… it’s humiliating and hot at the same time. I topped him, then he accidentally claimed something I’ve been guarding, then came all over my ass anyway. Messy. Real. Annoying and a mistake, but super hot.

I recognize I'm being too harsh. It was my fault, too. And pointing out he didn't pop my cherry might be a little petty. "It's okay, Tyler. I was careless, too. You have the honor of being the first man in my pussy. It's done."

He exhales, relieved but dazed.

I was ready to lose my virginity anyway. But not like this. I wanted it to be Ramya or Tanner. I'm so disappointed in myself. But at least Ramya can pop my cherry still. I don't need to tell her about this slip up. Tanner doesn't need to know since I just told him I was a virgin. How embarrassing.

Tyler wants to stay, but our very brief relationship has run its course. I send him home happy and turn my thoughts to Ramya and how I can put my new skills to use.